KR20080050522A - 헥사하이드로-사이클로헵타피라졸 카나비노이드 모듈레이터 - Google Patents

헥사하이드로-사이클로헵타피라졸 카나비노이드 모듈레이터 Download PDF

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Publication number: KR20080050522A
Authority: KR; South Korea
Prior art keywords: hexahydro; cycloheptapyrazole; phenyl; carboxylic acid; amide
Prior art date: 2005-09-23
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

KR1020087009625A

Other languages

English (en)

Korean (ko)

Inventor

피나 리오타

밍데 시아

후아준 루

멩 판

마이클 피. 왓터

Original Assignee

얀센 파마슈티카 엔.브이.

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2005-09-23

Filing date

2006-09-18

Publication date

2008-06-05

2006-09-18 Application filed by 얀센 파마슈티카 엔.브이. filed Critical 얀센 파마슈티카 엔.브이.

2008-06-05 Publication of KR20080050522A publication Critical patent/KR20080050522A/ko

Status Withdrawn legal-status Critical Current

Links

229930003827 cannabinoid Natural products 0.000 title abstract description 50
239000003557 cannabinoid Substances 0.000 title abstract description 50
YPKJAQSYNJIALU-UHFFFAOYSA-N 1,2,3,3a,4,5-hexahydrocyclohepta[c]pyrazole Chemical compound C1=CCCC2CNNC2=C1 YPKJAQSYNJIALU-UHFFFAOYSA-N 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 249
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 191
201000010099 disease Diseases 0.000 claims abstract description 96
208000035475 disorder Diseases 0.000 claims abstract description 95
238000000034 method Methods 0.000 claims abstract description 94
208000011580 syndromic disease Diseases 0.000 claims abstract description 89
230000001404 mediated effect Effects 0.000 claims abstract description 50
102000018208 Cannabinoid Receptor Human genes 0.000 claims abstract description 22
108050007331 Cannabinoid receptor Proteins 0.000 claims abstract description 22
239000000203 mixture Substances 0.000 claims description 115
229910052736 halogen Inorganic materials 0.000 claims description 107
150000002367 halogens Chemical class 0.000 claims description 107
125000000217 alkyl group Chemical group 0.000 claims description 104
-1 isomer Substances 0.000 claims description 94
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 84
125000000623 heterocyclic group Chemical group 0.000 claims description 81
125000003118 aryl group Chemical group 0.000 claims description 76
125000003545 alkoxy group Chemical group 0.000 claims description 60
125000000753 cycloalkyl group Chemical group 0.000 claims description 53
150000003839 salts Chemical class 0.000 claims description 51
239000000651 prodrug Substances 0.000 claims description 46
229940002612 prodrug Drugs 0.000 claims description 46
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 45
239000002207 metabolite Substances 0.000 claims description 39
102000005962 receptors Human genes 0.000 claims description 37
108020003175 receptors Proteins 0.000 claims description 37
125000005102 carbonylalkoxy group Chemical group 0.000 claims description 35
239000001257 hydrogen Substances 0.000 claims description 34
229910052739 hydrogen Inorganic materials 0.000 claims description 34
239000003433 contraceptive agent Substances 0.000 claims description 32
239000001961 anticonvulsive agent Substances 0.000 claims description 28
108010073366 CB1 Cannabinoid Receptor Proteins 0.000 claims description 27
102000009132 CB1 Cannabinoid Receptor Human genes 0.000 claims description 27
125000002947 alkylene group Chemical group 0.000 claims description 25
238000002648 combination therapy Methods 0.000 claims description 25
125000001118 alkylidene group Chemical group 0.000 claims description 24
108010073376 CB2 Cannabinoid Receptor Proteins 0.000 claims description 22
102000009135 CB2 Cannabinoid Receptor Human genes 0.000 claims description 22
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
150000002431 hydrogen Chemical class 0.000 claims description 22
239000003814 drug Substances 0.000 claims description 21
UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims description 20
239000000556 agonist Substances 0.000 claims description 20
230000001773 anti-convulsant effect Effects 0.000 claims description 20
229960003965 antiepileptics Drugs 0.000 claims description 20
125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 19
KJADKKWYZYXHBB-XBWDGYHZSA-N Topiramic acid Chemical group C1O[C@@]2(COS(N)(=O)=O)OC(C)(C)O[C@H]2[C@@H]2OC(C)(C)O[C@@H]21 KJADKKWYZYXHBB-XBWDGYHZSA-N 0.000 claims description 18
NIJJYAXOARWZEE-UHFFFAOYSA-N di-n-propyl-acetic acid Natural products CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 claims description 18
208000008589 Obesity Diseases 0.000 claims description 17
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 17
235000020824 obesity Nutrition 0.000 claims description 17
229940125425 inverse agonist Drugs 0.000 claims description 16
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102100033868 Cannabinoid receptor 1 Human genes 0.000 claims description 13
230000002254 contraceptive effect Effects 0.000 claims description 13
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
229960004394 topiramate Drugs 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
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206010012601 diabetes mellitus Diseases 0.000 claims description 12
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125000004043 oxo group Chemical group O=* 0.000 claims description 12
239000002469 receptor inverse agonist Substances 0.000 claims description 12
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 11
125000003282 alkyl amino group Chemical group 0.000 claims description 11
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 11
125000004104 aryloxy group Chemical group 0.000 claims description 11
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 10
208000002193 Pain Diseases 0.000 claims description 10
230000036407 pain Effects 0.000 claims description 10
RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 claims description 9
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
229960002870 gabapentin Drugs 0.000 claims description 9
PYZRQGJRPPTADH-UHFFFAOYSA-N lamotrigine Chemical compound NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl PYZRQGJRPPTADH-UHFFFAOYSA-N 0.000 claims description 9
229960000604 valproic acid Drugs 0.000 claims description 9
125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 8
229960001848 lamotrigine Drugs 0.000 claims description 8
238000006467 substitution reaction Methods 0.000 claims description 8
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206010010904 Convulsion Diseases 0.000 claims description 7
125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 7
FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 claims description 7
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125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 6
208000007101 Muscle Cramp Diseases 0.000 claims description 6
208000005392 Spasm Diseases 0.000 claims description 6
239000003555 cannabinoid 1 receptor antagonist Substances 0.000 claims description 6
229960000623 carbamazepine Drugs 0.000 claims description 6
230000004663 cell proliferation Effects 0.000 claims description 6
OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 claims description 6
230000004410 intraocular pressure Effects 0.000 claims description 6
210000000056 organ Anatomy 0.000 claims description 6
RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 claims description 5
208000010412 Glaucoma Diseases 0.000 claims description 5
208000019022 Mood disease Diseases 0.000 claims description 5
230000000391 smoking effect Effects 0.000 claims description 5
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201000009032 substance abuse Diseases 0.000 claims description 5
231100000736 substance abuse Toxicity 0.000 claims description 5
XBWOPGDJMAJJDG-SSDOTTSWSA-N (1r)-1-cyclohexylethanamine Chemical compound C[C@@H](N)C1CCCCC1 XBWOPGDJMAJJDG-SSDOTTSWSA-N 0.000 claims description 4
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 4
XYDZYAGTSSKICB-UHFFFAOYSA-N 8-[(3-chlorophenyl)methyl]-1-(2,4-dichlorophenyl)-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxylic acid Chemical compound C1CCCC=2C(C(=O)O)=NN(C=3C(=CC(Cl)=CC=3)Cl)C=2C1CC1=CC=CC(Cl)=C1 XYDZYAGTSSKICB-UHFFFAOYSA-N 0.000 claims description 4
RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims description 4
230000019771 cognition Effects 0.000 claims description 4
208000026278 immune system disease Diseases 0.000 claims description 4
208000027866 inflammatory disease Diseases 0.000 claims description 4
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229940127234 oral contraceptive Drugs 0.000 claims description 4
239000003539 oral contraceptive agent Substances 0.000 claims description 4
LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 claims description 4
239000000583 progesterone congener Substances 0.000 claims description 4
208000023504 respiratory system disease Diseases 0.000 claims description 4
HSWSMMPLNSVOKF-ACXJOVJBSA-N (8e)-1-(2,4-dichlorophenyl)-8-[(4-fluorophenyl)methylidene]-n-[(1r)-1-phenylethyl]-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CCCC\C2=C/C1=CC=C(F)C=C1 HSWSMMPLNSVOKF-ACXJOVJBSA-N 0.000 claims description 3
208000019430 Motor disease Diseases 0.000 claims description 3
OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 claims description 3
CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 claims description 3
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XBWOPGDJMAJJDG-ZETCQYMHSA-N (1s)-1-cyclohexylethanamine Chemical compound C[C@H](N)C1CCCCC1 XBWOPGDJMAJJDG-ZETCQYMHSA-N 0.000 claims description 2
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NRXVXRWBKHENQC-CAPFRKAQSA-N (8e)-1-(2,4-dichlorophenyl)-8-[(4-fluorophenyl)methylidene]-n-(1-pyridin-2-ylethyl)-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound C=1C=CC=NC=1C(C)NC(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CCCC\C2=C/C1=CC=C(F)C=C1 NRXVXRWBKHENQC-CAPFRKAQSA-N 0.000 claims description 2
CXLJXLFFSYBMMW-DYTRJAOYSA-N (8e)-1-(2,4-dichlorophenyl)-8-[(4-fluorophenyl)methylidene]-n-(2-phenylpropan-2-yl)-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CCCC\C2=C/C1=CC=C(F)C=C1 CXLJXLFFSYBMMW-DYTRJAOYSA-N 0.000 claims description 2
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NNELOXQSMGPYEO-OBGWFSINSA-N (8e)-1-(2,4-dichlorophenyl)-8-[(4-fluorophenyl)methylidene]-n-morpholin-4-yl-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(F)=CC=C1\C=C/1C(N(N=C2C(=O)NN3CCOCC3)C=3C(=CC(Cl)=CC=3)Cl)=C2CCCC\1 NNELOXQSMGPYEO-OBGWFSINSA-N 0.000 claims description 2
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YKGAWRIHDCKXST-HEHNFIMWSA-N (8e)-1-(2,4-dichlorophenyl)-8-[(4-methoxyphenyl)methylidene]-n-(1-pyridin-2-ylethyl)-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1\C=C/1C(N(N=C2C(=O)NC(C)C=3N=CC=CC=3)C=3C(=CC(Cl)=CC=3)Cl)=C2CCCC\1 YKGAWRIHDCKXST-HEHNFIMWSA-N 0.000 claims description 2
IXMMZOADQPAPEW-ZBJSNUHESA-N (8e)-1-(2,4-dichlorophenyl)-8-[(4-methoxyphenyl)methylidene]-n-(2-phenylpropan-2-yl)-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1\C=C/1C(N(N=C2C(=O)NC(C)(C)C=3C=CC=CC=3)C=3C(=CC(Cl)=CC=3)Cl)=C2CCCC\1 IXMMZOADQPAPEW-ZBJSNUHESA-N 0.000 claims description 2
MLHJWKGSGNLJBK-CAPFRKAQSA-N (8e)-1-(2,4-dichlorophenyl)-8-[(4-methoxyphenyl)methylidene]-n-(pyridin-2-ylmethyl)-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1\C=C/1C(N(N=C2C(=O)NCC=3N=CC=CC=3)C=3C(=CC(Cl)=CC=3)Cl)=C2CCCC\1 MLHJWKGSGNLJBK-CAPFRKAQSA-N 0.000 claims description 2
YCSPYZOZIBOGFJ-SXKRPYPPSA-N (8e)-1-(2,4-dichlorophenyl)-8-[(4-methoxyphenyl)methylidene]-n-[(1r)-1-phenylethyl]-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1\C=C/1C(N(N=C2C(=O)N[C@H](C)C=3C=CC=CC=3)C=3C(=CC(Cl)=CC=3)Cl)=C2CCCC\1 YCSPYZOZIBOGFJ-SXKRPYPPSA-N 0.000 claims description 2
YKGAWRIHDCKXST-OXMAITBSSA-N (8e)-1-(2,4-dichlorophenyl)-8-[(4-methoxyphenyl)methylidene]-n-[(1r)-1-pyridin-2-ylethyl]-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1\C=C/1C(N(N=C2C(=O)N[C@H](C)C=3N=CC=CC=3)C=3C(=CC(Cl)=CC=3)Cl)=C2CCCC\1 YKGAWRIHDCKXST-OXMAITBSSA-N 0.000 claims description 2
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JXRMKHDPVPYRCJ-DOIQENQNSA-N (8e)-8-[(3-chlorophenyl)methylidene]-n-[(1r)-2-hydroxy-1-phenylethyl]-4,5,6,7-tetrahydro-2h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@@H](CO)C=1C=CC=CC=1)C(=O)C1=NNC2=C1CCCC\C2=C/C1=CC=CC(Cl)=C1 JXRMKHDPVPYRCJ-DOIQENQNSA-N 0.000 claims description 2
AXQFDGPBAQGXGR-SLTDHEAWSA-N (8e)-8-[(3-fluorophenyl)methylidene]-n-[(1r)-2-hydroxy-1-phenylethyl]-1-methyl-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound C1([C@H](CO)NC(=O)C2=NN(C=3C(=C/C=4C=C(F)C=CC=4)/CCCCC=32)C)=CC=CC=C1 AXQFDGPBAQGXGR-SLTDHEAWSA-N 0.000 claims description 2
JOGIUVCRIDAYRZ-LVZFUZTISA-N (8e)-8-[(4-chlorophenyl)methylidene]-1-(2,4-dichlorophenyl)-n-(2-pyridin-2-ylethyl)-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1\C=C/1C(N(N=C2C(=O)NCCC=3N=CC=CC=3)C=3C(=CC(Cl)=CC=3)Cl)=C2CCCC\1 JOGIUVCRIDAYRZ-LVZFUZTISA-N 0.000 claims description 2
PFIHBCKVFQSIFT-XDJHFCHBSA-N (8e)-8-[(4-chlorophenyl)methylidene]-1-(2,4-dichlorophenyl)-n-(pyridin-2-ylmethyl)-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1\C=C/1C(N(N=C2C(=O)NCC=3N=CC=CC=3)C=3C(=CC(Cl)=CC=3)Cl)=C2CCCC\1 PFIHBCKVFQSIFT-XDJHFCHBSA-N 0.000 claims description 2
OHLVRVBYOAXOTF-HMMYKYKNSA-N (8e)-8-[(4-chlorophenyl)methylidene]-1-(2,4-dichlorophenyl)-n-(pyridin-4-ylmethyl)-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1\C=C/1C(N(N=C2C(=O)NCC=3C=CN=CC=3)C=3C(=CC(Cl)=CC=3)Cl)=C2CCCC\1 OHLVRVBYOAXOTF-HMMYKYKNSA-N 0.000 claims description 2
UNWKLOGBLMIAES-ACXJOVJBSA-N (8e)-8-[(4-chlorophenyl)methylidene]-1-(2,4-dichlorophenyl)-n-[(1r)-1-phenylethyl]-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CCCC\C2=C/C1=CC=C(Cl)C=C1 UNWKLOGBLMIAES-ACXJOVJBSA-N 0.000 claims description 2
UNWKLOGBLMIAES-WXNAFCGMSA-N (8e)-8-[(4-chlorophenyl)methylidene]-1-(2,4-dichlorophenyl)-n-[(1s)-1-phenylethyl]-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CCCC\C2=C/C1=CC=C(Cl)C=C1 UNWKLOGBLMIAES-WXNAFCGMSA-N 0.000 claims description 2
UTCRXRAVMCIYPM-HMMYKYKNSA-N (8e)-8-[(4-chlorophenyl)methylidene]-1-(2,4-dichlorophenyl)-n-[(4-sulfamoylphenyl)methyl]-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CCCC\C2=C/C1=CC=C(Cl)C=C1 UTCRXRAVMCIYPM-HMMYKYKNSA-N 0.000 claims description 2
KHRNIWOWMWXLOT-OBGWFSINSA-N (8e)-8-[(4-chlorophenyl)methylidene]-1-(2,4-dichlorophenyl)-n-morpholin-4-yl-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1\C=C/1C(N(N=C2C(=O)NN3CCOCC3)C=3C(=CC(Cl)=CC=3)Cl)=C2CCCC\1 KHRNIWOWMWXLOT-OBGWFSINSA-N 0.000 claims description 2
NJKGCGKEHRGKDM-KNTRCKAVSA-N (8e)-8-[(4-chlorophenyl)methylidene]-1-(2,4-dichlorophenyl)-n-piperidin-1-yl-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1\C=C/1C(N(N=C2C(=O)NN3CCCCC3)C=3C(=CC(Cl)=CC=3)Cl)=C2CCCC\1 NJKGCGKEHRGKDM-KNTRCKAVSA-N 0.000 claims description 2
HTHYPTKYURAYKB-OBGWFSINSA-N (8e)-8-[(4-chlorophenyl)methylidene]-1-(2,4-dichlorophenyl)-n-pyridin-2-yl-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1\C=C/1C(N(N=C2C(=O)NC=3N=CC=CC=3)C=3C(=CC(Cl)=CC=3)Cl)=C2CCCC\1 HTHYPTKYURAYKB-OBGWFSINSA-N 0.000 claims description 2
ZFGYYLMARIIKDN-ACXJOVJBSA-N (8e)-8-[(4-chlorophenyl)methylidene]-n-[(1r)-1-cyclohexylethyl]-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@H](C)C1CCCCC1)C(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CCCC\C2=C/C1=CC=C(Cl)C=C1 ZFGYYLMARIIKDN-ACXJOVJBSA-N 0.000 claims description 2
JCNNLBDLRJMFEQ-PAYQVUOSSA-N (8e)-8-[(4-chlorophenyl)methylidene]-n-[(1r)-1-cyclohexylethyl]-1-(4-sulfamoylphenyl)-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@H](C)C1CCCCC1)C(=O)C1=NN(C=2C=CC(=CC=2)S(N)(=O)=O)C2=C1CCCC\C2=C/C1=CC=C(Cl)C=C1 JCNNLBDLRJMFEQ-PAYQVUOSSA-N 0.000 claims description 2
VNEXKXJYRVHABV-PAYQVUOSSA-N (8e)-8-[(4-chlorophenyl)methylidene]-n-[(1r)-1-cyclohexylethyl]-1-pyridin-4-yl-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@H](C)C1CCCCC1)C(=O)C1=NN(C=2C=CN=CC=2)C2=C1CCCC\C2=C/C1=CC=C(Cl)C=C1 VNEXKXJYRVHABV-PAYQVUOSSA-N 0.000 claims description 2
SCTAUPJHLGHZND-ORMOWBNMSA-N (8e)-8-[(4-chlorophenyl)methylidene]-n-[(1r)-1-cyclohexylethyl]-4,5,6,7-tetrahydro-2h-cyclohepta[c]pyrazole-3-carboxamide Chemical class N([C@H](C)C1CCCCC1)C(=O)C1=NNC2=C1CCCC\C2=C/C1=CC=C(Cl)C=C1 SCTAUPJHLGHZND-ORMOWBNMSA-N 0.000 claims description 2
PUJMKEIQSGPEHD-PAYQVUOSSA-N (8e)-8-[(4-chlorophenyl)methylidene]-n-[(1r)-1-phenylethyl]-1-(4-sulfamoylphenyl)-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(=O)C1=NN(C=2C=CC(=CC=2)S(N)(=O)=O)C2=C1CCCC\C2=C/C1=CC=C(Cl)C=C1 PUJMKEIQSGPEHD-PAYQVUOSSA-N 0.000 claims description 2
OPTYZTBDVAYYFI-ORMOWBNMSA-N (8e)-8-[(4-chlorophenyl)methylidene]-n-[(1r)-1-phenylethyl]-4,5,6,7-tetrahydro-2h-cyclohepta[c]pyrazole-3-carboxamide Chemical class N([C@H](C)C=1C=CC=CC=1)C(=O)C1=NNC2=C1CCCC\C2=C/C1=CC=C(Cl)C=C1 OPTYZTBDVAYYFI-ORMOWBNMSA-N 0.000 claims description 2
LLBFTFFJABJIEV-TVADFSRQSA-N (8e)-8-[(4-chlorophenyl)methylidene]-n-[(1r)-2-hydroxy-1-phenylethyl]-4,5,6,7-tetrahydro-2h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@@H](CO)C=1C=CC=CC=1)C(=O)C1=NNC2=C1CCCC\C2=C/C1=CC=C(Cl)C=C1 LLBFTFFJABJIEV-TVADFSRQSA-N 0.000 claims description 2
ZFGYYLMARIIKDN-WXNAFCGMSA-N (8e)-8-[(4-chlorophenyl)methylidene]-n-[(1s)-1-cyclohexylethyl]-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@@H](C)C1CCCCC1)C(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CCCC\C2=C/C1=CC=C(Cl)C=C1 ZFGYYLMARIIKDN-WXNAFCGMSA-N 0.000 claims description 2
VNEXKXJYRVHABV-LOKSUBMMSA-N (8e)-8-[(4-chlorophenyl)methylidene]-n-[(1s)-1-cyclohexylethyl]-1-pyridin-4-yl-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@@H](C)C1CCCCC1)C(=O)C1=NN(C=2C=CN=CC=2)C2=C1CCCC\C2=C/C1=CC=C(Cl)C=C1 VNEXKXJYRVHABV-LOKSUBMMSA-N 0.000 claims description 2
SCTAUPJHLGHZND-DAMBIUFKSA-N (8e)-8-[(4-chlorophenyl)methylidene]-n-[(1s)-1-cyclohexylethyl]-4,5,6,7-tetrahydro-2h-cyclohepta[c]pyrazole-3-carboxamide Chemical class N([C@@H](C)C1CCCCC1)C(=O)C1=NNC2=C1CCCC\C2=C/C1=CC=C(Cl)C=C1 SCTAUPJHLGHZND-DAMBIUFKSA-N 0.000 claims description 2
OPTYZTBDVAYYFI-DAMBIUFKSA-N (8e)-8-[(4-chlorophenyl)methylidene]-n-[(1s)-1-phenylethyl]-4,5,6,7-tetrahydro-2h-cyclohepta[c]pyrazole-3-carboxamide Chemical class N([C@@H](C)C=1C=CC=CC=1)C(=O)C1=NNC2=C1CCCC\C2=C/C1=CC=C(Cl)C=C1 OPTYZTBDVAYYFI-DAMBIUFKSA-N 0.000 claims description 2
UWDQCBHQOWWERH-FYWRMAATSA-N (8e)-8-[(4-chlorophenyl)methylidene]-n-morpholin-4-yl-4,5,6,7-tetrahydro-2h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1\C=C/1C(NN=C2C(=O)NN3CCOCC3)=C2CCCC\1 UWDQCBHQOWWERH-FYWRMAATSA-N 0.000 claims description 2
AFPXKROAMLUHBC-JQIJEIRASA-N (8e)-8-[(4-chlorophenyl)methylidene]-n-piperidin-1-yl-4,5,6,7-tetrahydro-2h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1\C=C/1C(NN=C2C(=O)NN3CCCCC3)=C2CCCC\1 AFPXKROAMLUHBC-JQIJEIRASA-N 0.000 claims description 2
NEHQZHJGSBWECQ-HMMYKYKNSA-N (8e)-n-(3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-1-(2,4-dichlorophenyl)-8-[(4-methoxyphenyl)methylidene]-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1\C=C/1C(N(N=C2C(=O)NN3CC4CCCC4C3)C=3C(=CC(Cl)=CC=3)Cl)=C2CCCC\1 NEHQZHJGSBWECQ-HMMYKYKNSA-N 0.000 claims description 2
UVDFABZBPRYCGN-ACXJOVJBSA-N (8e)-n-[(1r)-1-cyclohexylethyl]-1-(2,4-dichlorophenyl)-8-[(4-fluorophenyl)methylidene]-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@H](C)C1CCCCC1)C(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CCCC\C2=C/C1=CC=C(F)C=C1 UVDFABZBPRYCGN-ACXJOVJBSA-N 0.000 claims description 2
KNDXRAIHZDRNSB-SXKRPYPPSA-N (8e)-n-[(1r)-1-cyclohexylethyl]-1-(2,4-dichlorophenyl)-8-[(4-methoxyphenyl)methylidene]-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1\C=C/1C(N(N=C2C(=O)N[C@H](C)C3CCCCC3)C=3C(=CC(Cl)=CC=3)Cl)=C2CCCC\1 KNDXRAIHZDRNSB-SXKRPYPPSA-N 0.000 claims description 2
UVDFABZBPRYCGN-WXNAFCGMSA-N (8e)-n-[(1s)-1-cyclohexylethyl]-1-(2,4-dichlorophenyl)-8-[(4-fluorophenyl)methylidene]-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@@H](C)C1CCCCC1)C(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CCCC\C2=C/C1=CC=C(F)C=C1 UVDFABZBPRYCGN-WXNAFCGMSA-N 0.000 claims description 2
ZMERVBPVJUSXDQ-LTGZKZEYSA-N (8e)-n-[1-(4-chlorophenyl)ethyl]-8-[(4-chlorophenyl)methylidene]-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(C)NC(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C2=C1CCCC\C2=C/C1=CC=C(Cl)C=C1 ZMERVBPVJUSXDQ-LTGZKZEYSA-N 0.000 claims description 2
GUXIGRIJAMKJHK-ZJQZWDJDSA-N (e)-2-[(8e)-8-[(4-chlorophenyl)methylidene]-4,5,6,7-tetrahydro-2h-cyclohepta[c]pyrazol-3-yl]-n-[(1s)-1-phenylethyl]ethenesulfonamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)S(=O)(=O)\C=C\C1=NNC2=C1CCCC\C2=C/C1=CC=C(Cl)C=C1 GUXIGRIJAMKJHK-ZJQZWDJDSA-N 0.000 claims description 2
JWSWKEGXIIFZBC-AAEWGKPLSA-N (e)-2-[1-cyclohexyl-8-[(3-fluorophenyl)methyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazol-3-yl]-n-[(1s)-1-phenylethyl]ethenesulfonamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)S(=O)(=O)\C=C\C(C=1CCCCC(CC=2C=C(F)C=CC=2)C=11)=NN1C1CCCCC1 JWSWKEGXIIFZBC-AAEWGKPLSA-N 0.000 claims description 2
LRZPQDXPIRWVRC-PTULCPQNSA-N (e)-2-[8-[(3-chlorophenyl)methyl]-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazol-3-yl]-n-[(1s)-1-phenylethyl]ethenesulfonamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)S(=O)(=O)\C=C\C(C=1CCCC2)=NNC=1C2CC1=CC=CC(Cl)=C1 LRZPQDXPIRWVRC-PTULCPQNSA-N 0.000 claims description 2
ZJNQGLZHOIOWFU-PTULCPQNSA-N (e)-2-[8-[(3-fluorophenyl)methyl]-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazol-3-yl]-n-[(1s)-1-phenylethyl]ethenesulfonamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)S(=O)(=O)\C=C\C(C=1CCCC2)=NNC=1C2CC1=CC=CC(F)=C1 ZJNQGLZHOIOWFU-PTULCPQNSA-N 0.000 claims description 2
LUUNFDBNPNJRCI-XKFIIDRESA-N (e)-2-[8-[(3-fluorophenyl)methyl]-1-methyl-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazol-3-yl]-n-[(1s)-1-phenylethyl]ethenesulfonamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)S(=O)(=O)\C=C\C(C=1CCCC2)=NN(C)C=1C2CC1=CC=CC(F)=C1 LUUNFDBNPNJRCI-XKFIIDRESA-N 0.000 claims description 2
YVKHCPJFKYFTQR-NLYRQODGSA-N (e)-2-[8-[(4-fluorophenyl)methyl]-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazol-3-yl]-n-[(1s)-1-phenylethyl]ethenesulfonamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)S(=O)(=O)\C=C\C(C=1CCCC2)=NNC=1C2CC1=CC=C(F)C=C1 YVKHCPJFKYFTQR-NLYRQODGSA-N 0.000 claims description 2
JGMLFEHHSMTFHO-BKZNFVNUSA-N (e)-2-[8-[(4-fluorophenyl)methyl]-1-methyl-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazol-3-yl]-n-[(1s)-1-phenylethyl]ethenesulfonamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)S(=O)(=O)\C=C\C(C=1CCCC2)=NN(C)C=1C2CC1=CC=C(F)C=C1 JGMLFEHHSMTFHO-BKZNFVNUSA-N 0.000 claims description 2
AWJFATYFKGCVJQ-ZHACJKMWSA-N (e)-2-[8-[(4-fluorophenyl)methyl]-1-methyl-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazol-3-yl]ethenesulfonic acid Chemical compound C1=2N(C)N=C(\C=C\S(O)(=O)=O)C=2CCCCC1CC1=CC=C(F)C=C1 AWJFATYFKGCVJQ-ZHACJKMWSA-N 0.000 claims description 2
QVMVAWAAQRTCHF-UHFFFAOYSA-N 1,8-bis[(4-chlorophenyl)methyl]-n-cyclobutyl-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1CC1C(N(CC=2C=CC(Cl)=CC=2)N=C2C(=O)NC3CCC3)=C2CCCC1 QVMVAWAAQRTCHF-UHFFFAOYSA-N 0.000 claims description 2
JPIHWGOSBMACKK-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-8-[(3-fluorophenyl)methyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxylic acid Chemical compound C1CCCC=2C(C(=O)O)=NN(C=3C(=CC(Cl)=CC=3)Cl)C=2C1CC1=CC=CC(F)=C1 JPIHWGOSBMACKK-UHFFFAOYSA-N 0.000 claims description 2
NHWGBIISVQBSSX-UQKFXCHMSA-N 1-(2,4-dichlorophenyl)-8-[(3-fluorophenyl)methyl]-n-[(3s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@@H]1C(C)(C)C2CCC1(C2)C)C(=O)C(C=1CCCC2)=NN(C=3C(=CC(Cl)=CC=3)Cl)C=1C2CC1=CC=CC(F)=C1 NHWGBIISVQBSSX-UQKFXCHMSA-N 0.000 claims description 2
AEYFDFDBNLOZEB-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-8-[(3-fluorophenyl)methyl]-n-piperidin-1-yl-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound FC1=CC=CC(CC2C=3N(N=C(C=3CCCC2)C(=O)NN2CCCCC2)C=2C(=CC(Cl)=CC=2)Cl)=C1 AEYFDFDBNLOZEB-UHFFFAOYSA-N 0.000 claims description 2
QJFLGJGXIALCPH-UQKFXCHMSA-N 1-(2,4-difluorophenyl)-8-[(3-fluorophenyl)methyl]-n-[(3s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@@H]1C(C)(C)C2CCC1(C2)C)C(=O)C(C=1CCCC2)=NN(C=3C(=CC(F)=CC=3)F)C=1C2CC1=CC=CC(F)=C1 QJFLGJGXIALCPH-UQKFXCHMSA-N 0.000 claims description 2
JXJZVMCPWPVMFI-UQKFXCHMSA-N 1-(2,4-difluorophenyl)-8-[(4-fluorophenyl)methyl]-n-[(3s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@@H]1C(C)(C)C2CCC1(C2)C)C(=O)C(C=1CCCC2)=NN(C=3C(=CC(F)=CC=3)F)C=1C2CC1=CC=C(F)C=C1 JXJZVMCPWPVMFI-UQKFXCHMSA-N 0.000 claims description 2
USUHRXUTAZCTJB-CHQVSRGASA-N 1-benzyl-8-phenyl-n-[(1s)-1-phenylethyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(=O)C(C=1CCCCC(C=11)C=2C=CC=CC=2)=NN1CC1=CC=CC=C1 USUHRXUTAZCTJB-CHQVSRGASA-N 0.000 claims description 2
VVCWCTWDHLGKLL-GRYITMIPSA-N 1-benzyl-8-phenyl-n-[(3s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@@H]1C(C)(C)C2CCC1(C2)C)C(=O)C(C=1CCCCC(C=11)C=2C=CC=CC=2)=NN1CC1=CC=CC=C1 VVCWCTWDHLGKLL-GRYITMIPSA-N 0.000 claims description 2
DFYAAJYDCXEALH-XEGCMXMBSA-N 1-cyclohexyl-8-[(3-fluorophenyl)methyl]-n-[(1s)-1-phenylethyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical class N([C@@H](C)C=1C=CC=CC=1)C(=O)C(C=1CCCCC(CC=2C=C(F)C=CC=2)C=11)=NN1C1CCCCC1 DFYAAJYDCXEALH-XEGCMXMBSA-N 0.000 claims description 2
MQPDKUVOZPGUEG-WLTWJZIYSA-N 1-cyclohexyl-8-[(3-fluorophenyl)methyl]-n-[(3s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@@H]1C(C)(C)C2CCC1(C2)C)C(=O)C(C=1CCCCC(CC=2C=C(F)C=CC=2)C=11)=NN1C1CCCCC1 MQPDKUVOZPGUEG-WLTWJZIYSA-N 0.000 claims description 2
BRWORVWMVVWQIF-XEGCMXMBSA-N 1-cyclohexyl-8-[(4-fluorophenyl)methyl]-n-[(1s)-1-phenylethyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical class N([C@@H](C)C=1C=CC=CC=1)C(=O)C(C=1CCCCC(CC=2C=CC(F)=CC=2)C=11)=NN1C1CCCCC1 BRWORVWMVVWQIF-XEGCMXMBSA-N 0.000 claims description 2
KESIBANXYVTAQL-WLTWJZIYSA-N 1-cyclohexyl-8-[(4-fluorophenyl)methyl]-n-[(3s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@@H]1C(C)(C)C2CCC1(C2)C)C(=O)C(C=1CCCCC(CC=2C=CC(F)=CC=2)C=11)=NN1C1CCCCC1 KESIBANXYVTAQL-WLTWJZIYSA-N 0.000 claims description 2
ZJWAPDHYNZTAIK-UHFFFAOYSA-N 1-cyclohexyl-8-[(4-fluorophenyl)methyl]-n-[[4-(trifluoromethyl)phenyl]methyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(F)=CC=C1CC1C(N(C2CCCCC2)N=C2C(=O)NCC=3C=CC(=CC=3)C(F)(F)F)=C2CCCC1 ZJWAPDHYNZTAIK-UHFFFAOYSA-N 0.000 claims description 2
QDBUTTPSEAWSJH-UHFFFAOYSA-N 1-cyclohexyl-n-cyclopentyl-8-[(4-fluorophenyl)methyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(F)=CC=C1CC1C(N(C2CCCCC2)N=C2C(=O)NC3CCCC3)=C2CCCC1 QDBUTTPSEAWSJH-UHFFFAOYSA-N 0.000 claims description 2
SNEODCVZIIYWMD-WJZIVOKESA-N 8-[(2-chlorophenyl)methyl]-1-methyl-n-[(3s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=2N(C)N=C(C(=O)N[C@@H]3C(C4CCC3(C)C4)(C)C)C=2CCCCC1CC1=CC=CC=C1Cl SNEODCVZIIYWMD-WJZIVOKESA-N 0.000 claims description 2
JPRPJEFGNWQHDG-UQKFXCHMSA-N 8-[(3-chlorophenyl)methyl]-1-(2,4-dichlorophenyl)-n-[(3s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@@H]1C(C)(C)C2CCC1(C2)C)C(=O)C(C=1CCCC2)=NN(C=3C(=CC(Cl)=CC=3)Cl)C=1C2CC1=CC=CC(Cl)=C1 JPRPJEFGNWQHDG-UQKFXCHMSA-N 0.000 claims description 2
WGZVEFSKJMPLNR-XEGCMXMBSA-N 8-[(3-chlorophenyl)methyl]-1-cyclohexyl-n-[(1s)-1-phenylethyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical class N([C@@H](C)C=1C=CC=CC=1)C(=O)C(C=1CCCCC(CC=2C=C(Cl)C=CC=2)C=11)=NN1C1CCCCC1 WGZVEFSKJMPLNR-XEGCMXMBSA-N 0.000 claims description 2
XFJSCCHOOFTQRX-ZYZRXSCRSA-N 8-[(3-chlorophenyl)methyl]-n-[(1r)-2-hydroxy-1-phenylethyl]-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazole-3-carboxamide Chemical class N([C@@H](CO)C=1C=CC=CC=1)C(=O)C(C=1CCCC2)=NNC=1C2CC1=CC=CC(Cl)=C1 XFJSCCHOOFTQRX-ZYZRXSCRSA-N 0.000 claims description 2
XFJSCCHOOFTQRX-BDPMCISCSA-N 8-[(3-chlorophenyl)methyl]-n-[(1s)-2-hydroxy-1-phenylethyl]-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazole-3-carboxamide Chemical class N([C@H](CO)C=1C=CC=CC=1)C(=O)C(C=1CCCC2)=NNC=1C2CC1=CC=CC(Cl)=C1 XFJSCCHOOFTQRX-BDPMCISCSA-N 0.000 claims description 2
DOJUWYZZERGHKT-VGAJERRHSA-N 8-[(3-chlorophenyl)methyl]-n-[(2r)-1-hydroxy-3-phenylpropan-2-yl]-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazole-3-carboxamide Chemical class C([C@H](CO)NC(=O)C=1C=2CCCCC(CC=3C=C(Cl)C=CC=3)C=2NN=1)C1=CC=CC=C1 DOJUWYZZERGHKT-VGAJERRHSA-N 0.000 claims description 2
KPICAFHGTMWFKY-JFGZAKSSSA-N 8-[(3-chlorophenyl)methyl]-n-[(2r)-1-hydroxy-3-phenylpropan-2-yl]-1-[4-(trifluoromethyl)pyrimidin-2-yl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound C([C@H](CO)NC(=O)C=1C=2CCCCC(CC=3C=C(Cl)C=CC=3)C=2N(N=1)C=1N=C(C=CN=1)C(F)(F)F)C1=CC=CC=C1 KPICAFHGTMWFKY-JFGZAKSSSA-N 0.000 claims description 2
DOJUWYZZERGHKT-QWAKEFERSA-N 8-[(3-chlorophenyl)methyl]-n-[(2s)-1-hydroxy-3-phenylpropan-2-yl]-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazole-3-carboxamide Chemical class C([C@@H](CO)NC(=O)C=1C=2CCCCC(CC=3C=C(Cl)C=CC=3)C=2NN=1)C1=CC=CC=C1 DOJUWYZZERGHKT-QWAKEFERSA-N 0.000 claims description 2
WYHGJZJVLWCXJE-UHFFFAOYSA-N 8-[(4-chlorophenyl)methyl]-1-(2,4-dichlorophenyl)-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxylic acid Chemical compound C1CCCC=2C(C(=O)O)=NN(C=3C(=CC(Cl)=CC=3)Cl)C=2C1CC1=CC=C(Cl)C=C1 WYHGJZJVLWCXJE-UHFFFAOYSA-N 0.000 claims description 2
CFVVAVVUUUNYHD-WLTWJZIYSA-N 8-[(4-chlorophenyl)methyl]-1-cyclohexyl-n-[(3s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@@H]1C(C)(C)C2CCC1(C2)C)C(=O)C(C=1CCCCC(CC=2C=CC(Cl)=CC=2)C=11)=NN1C1CCCCC1 CFVVAVVUUUNYHD-WLTWJZIYSA-N 0.000 claims description 2
METHDBDEMUHHDV-UHFFFAOYSA-N 8-[(4-chlorophenyl)methyl]-n-cyclobutyl-1-(2,4-dichlorophenyl)-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1CC1C(N(N=C2C(=O)NC3CCC3)C=3C(=CC(Cl)=CC=3)Cl)=C2CCCC1 METHDBDEMUHHDV-UHFFFAOYSA-N 0.000 claims description 2
FZINAXIAUSGRGQ-DYTRJAOYSA-N [(8e)-1-(2,4-dichlorophenyl)-8-[(4-fluorophenyl)methylidene]-4,5,6,7-tetrahydrocyclohepta[c]pyrazol-3-yl]-(2-pyridin-2-ylpyrrolidin-1-yl)methanone Chemical compound C1=CC(F)=CC=C1\C=C/1C(N(N=C2C(=O)N3C(CCC3)C=3N=CC=CC=3)C=3C(=CC(Cl)=CC=3)Cl)=C2CCCC\1 FZINAXIAUSGRGQ-DYTRJAOYSA-N 0.000 claims description 2
229940011871 estrogen Drugs 0.000 claims description 2
239000000262 estrogen Substances 0.000 claims description 2
VRWOFXZIYVOUPD-GQXFROSMSA-N ethyl (2r,3s)-3-[[1-(2,4-difluorophenyl)-8-[(3-fluorophenyl)methyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carbonyl]amino]bicyclo[2.2.1]heptane-2-carboxylate Chemical compound N([C@H]1C2CCC(C2)[C@H]1C(=O)OCC)C(=O)C(C=1CCCC2)=NN(C=3C(=CC(F)=CC=3)F)C=1C2CC1=CC=CC(F)=C1 VRWOFXZIYVOUPD-GQXFROSMSA-N 0.000 claims description 2
MQAOILSZHBBTOI-GQXFROSMSA-N ethyl (2r,3s)-3-[[1-(2,4-difluorophenyl)-8-[(4-fluorophenyl)methyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carbonyl]amino]bicyclo[2.2.1]heptane-2-carboxylate Chemical compound N([C@H]1C2CCC(C2)[C@H]1C(=O)OCC)C(=O)C(C=1CCCC2)=NN(C=3C(=CC(F)=CC=3)F)C=1C2CC1=CC=C(F)C=C1 MQAOILSZHBBTOI-GQXFROSMSA-N 0.000 claims description 2
DISYYECMYSYQCR-BFPPLCHTSA-N ethyl (2r,3s)-3-[[1-cyclohexyl-8-[(4-fluorophenyl)methyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carbonyl]amino]bicyclo[2.2.1]heptane-2-carboxylate Chemical compound N([C@H]1C2CCC(C2)[C@H]1C(=O)OCC)C(=O)C(C=1CCCCC(CC=2C=CC(F)=CC=2)C=11)=NN1C1CCCCC1 DISYYECMYSYQCR-BFPPLCHTSA-N 0.000 claims description 2
NYTSHWHHKZXSAG-MKRMIXIUSA-N methyl (2r)-2-[[(8e)-8-[(3-chlorophenyl)methylidene]-4,5,6,7-tetrahydro-2h-cyclohepta[c]pyrazole-3-carbonyl]amino]-3-(4-fluorophenyl)propanoate Chemical compound C([C@H](C(=O)OC)NC(=O)C=1C2=C(C(/CCCC2)=C/C=2C=C(Cl)C=CC=2)NN=1)C1=CC=C(F)C=C1 NYTSHWHHKZXSAG-MKRMIXIUSA-N 0.000 claims description 2
YYFIWSHVJPMONV-OVWUPXBPSA-N methyl (2r)-2-[[(8e)-8-[(4-chlorophenyl)methylidene]-4,5,6,7-tetrahydro-2h-cyclohepta[c]pyrazole-3-carbonyl]amino]-3-(4-fluorophenyl)propanoate Chemical compound C([C@H](C(=O)OC)NC(=O)C=1C2=C(C(/CCCC2)=C/C=2C=CC(Cl)=CC=2)NN=1)C1=CC=C(F)C=C1 YYFIWSHVJPMONV-OVWUPXBPSA-N 0.000 claims description 2
RBWFSFBQOOQCBO-JIPXPUAJSA-N methyl (2r)-2-[[(8r)-1-(2,4-dichlorophenyl)-8-[(3-fluorophenyl)methyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carbonyl]amino]-3-(4-fluorophenyl)propanoate Chemical compound C([C@H](C(=O)OC)NC(=O)C=1C=2CCCC[C@H](CC=3C=C(F)C=CC=3)C=2N(N=1)C=1C(=CC(Cl)=CC=1)Cl)C1=CC=C(F)C=C1 RBWFSFBQOOQCBO-JIPXPUAJSA-N 0.000 claims description 2
RBWFSFBQOOQCBO-KDYSTLNUSA-N methyl (2r)-2-[[(8s)-1-(2,4-dichlorophenyl)-8-[(3-fluorophenyl)methyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carbonyl]amino]-3-(4-fluorophenyl)propanoate Chemical compound C([C@H](C(=O)OC)NC(=O)C=1C=2CCCC[C@@H](CC=3C=C(F)C=CC=3)C=2N(N=1)C=1C(=CC(Cl)=CC=1)Cl)C1=CC=C(F)C=C1 RBWFSFBQOOQCBO-KDYSTLNUSA-N 0.000 claims description 2
XAWMMCUQSFRGKK-IAIRZMIISA-N methyl (2r)-2-[[1-(2,4-dichlorophenyl)-8-[(3-fluorophenyl)methyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carbonyl]amino]-3-(4-hydroxyphenyl)propanoate Chemical compound C([C@H](C(=O)OC)NC(=O)C=1C=2CCCCC(CC=3C=C(F)C=CC=3)C=2N(N=1)C=1C(=CC(Cl)=CC=1)Cl)C1=CC=C(O)C=C1 XAWMMCUQSFRGKK-IAIRZMIISA-N 0.000 claims description 2
KCZFNNWZALSELB-IAIRZMIISA-N methyl (2r)-2-[[1-(2,4-difluorophenyl)-8-[(4-fluorophenyl)methyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carbonyl]amino]-3-(4-hydroxyphenyl)propanoate Chemical compound C([C@H](C(=O)OC)NC(=O)C=1C=2CCCCC(CC=3C=CC(F)=CC=3)C=2N(N=1)C=1C(=CC(F)=CC=1)F)C1=CC=C(O)C=C1 KCZFNNWZALSELB-IAIRZMIISA-N 0.000 claims description 2
BJJZHFVIIFSCBA-GBAZGAGXSA-N methyl (2r)-2-[[1-cyclohexyl-8-[(3-fluorophenyl)methyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carbonyl]amino]-3-(4-hydroxyphenyl)propanoate Chemical compound C([C@H](C(=O)OC)NC(=O)C=1C=2CCCCC(CC=3C=C(F)C=CC=3)C=2N(C2CCCCC2)N=1)C1=CC=C(O)C=C1 BJJZHFVIIFSCBA-GBAZGAGXSA-N 0.000 claims description 2
VMFZKKZPGMAQOC-GBAZGAGXSA-N methyl (2r)-2-[[1-cyclohexyl-8-[(4-fluorophenyl)methyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carbonyl]amino]-3-(4-hydroxyphenyl)propanoate Chemical compound C([C@H](C(=O)OC)NC(=O)C=1C=2CCCCC(CC=3C=CC(F)=CC=3)C=2N(C2CCCCC2)N=1)C1=CC=C(O)C=C1 VMFZKKZPGMAQOC-GBAZGAGXSA-N 0.000 claims description 2
GADTVLHYYWCNIB-IAIRZMIISA-N methyl (2r)-2-[[8-[(3-chlorophenyl)methyl]-1-(2,4-dichlorophenyl)-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carbonyl]amino]-3-(4-fluorophenyl)propanoate Chemical compound C([C@H](C(=O)OC)NC(=O)C=1C=2CCCCC(CC=3C=C(Cl)C=CC=3)C=2N(N=1)C=1C(=CC(Cl)=CC=1)Cl)C1=CC=C(F)C=C1 GADTVLHYYWCNIB-IAIRZMIISA-N 0.000 claims description 2
QJMLOXYYGNITLR-IAIRZMIISA-N methyl (2r)-2-[[8-[(3-chlorophenyl)methyl]-1-(2,4-dichlorophenyl)-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carbonyl]amino]-3-(4-hydroxyphenyl)propanoate Chemical compound C([C@H](C(=O)OC)NC(=O)C=1C=2CCCCC(CC=3C=C(Cl)C=CC=3)C=2N(N=1)C=1C(=CC(Cl)=CC=1)Cl)C1=CC=C(O)C=C1 QJMLOXYYGNITLR-IAIRZMIISA-N 0.000 claims description 2
SYKNPFMXUDZUBX-CMYVBNMBSA-N methyl (2r)-3-(4-fluorophenyl)-2-[[(8e)-8-[(3-fluorophenyl)methylidene]-1-methyl-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carbonyl]amino]propanoate Chemical compound C([C@H](C(=O)OC)NC(=O)C=1C2=C(C(/CCCC2)=C/C=2C=C(F)C=CC=2)N(C)N=1)C1=CC=C(F)C=C1 SYKNPFMXUDZUBX-CMYVBNMBSA-N 0.000 claims description 2
NYTSHWHHKZXSAG-CAVPUYEOSA-N methyl (2s)-2-[[(8e)-8-[(3-chlorophenyl)methylidene]-4,5,6,7-tetrahydro-2h-cyclohepta[c]pyrazole-3-carbonyl]amino]-3-(4-fluorophenyl)propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)C=1C2=C(C(/CCCC2)=C/C=2C=C(Cl)C=CC=2)NN=1)C1=CC=C(F)C=C1 NYTSHWHHKZXSAG-CAVPUYEOSA-N 0.000 claims description 2
YYFIWSHVJPMONV-RRXSNJIPSA-N methyl (2s)-2-[[(8e)-8-[(4-chlorophenyl)methylidene]-4,5,6,7-tetrahydro-2h-cyclohepta[c]pyrazole-3-carbonyl]amino]-3-(4-fluorophenyl)propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)C=1C2=C(C(/CCCC2)=C/C=2C=CC(Cl)=CC=2)NN=1)C1=CC=C(F)C=C1 YYFIWSHVJPMONV-RRXSNJIPSA-N 0.000 claims description 2
GCVQLVHMRZOMFW-WOKNPCPGSA-N methyl (2s)-2-[[1-cyclohexyl-8-[(4-fluorophenyl)methyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carbonyl]amino]-3-(4-fluorophenyl)propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)C=1C=2CCCCC(CC=3C=CC(F)=CC=3)C=2N(C2CCCCC2)N=1)C1=CC=C(F)C=C1 GCVQLVHMRZOMFW-WOKNPCPGSA-N 0.000 claims description 2
SYKNPFMXUDZUBX-YHSGTQGLSA-N methyl (2s)-3-(4-fluorophenyl)-2-[[(8e)-8-[(3-fluorophenyl)methylidene]-1-methyl-4,5,6,7-tetrahydrocyclohepta[c]pyrazole-3-carbonyl]amino]propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)C=1C2=C(C(/CCCC2)=C/C=2C=C(F)C=CC=2)N(C)N=1)C1=CC=C(F)C=C1 SYKNPFMXUDZUBX-YHSGTQGLSA-N 0.000 claims description 2
KYACRLHKRKYDNI-UHFFFAOYSA-N n-(1-adamantyl)-8-[(3-chlorophenyl)methyl]-1-cyclohexyl-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound ClC1=CC=CC(CC2C=3N(C4CCCCC4)N=C(C=3CCCC2)C(=O)NC23CC4CC(CC(C4)C2)C3)=C1 KYACRLHKRKYDNI-UHFFFAOYSA-N 0.000 claims description 2
DQMOKQSNSQFVFS-UHFFFAOYSA-N n-(2-adamantyl)-8-[(4-chlorophenyl)methyl]-1-cyclohexyl-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1CC1C(N(C2CCCCC2)N=C2C(=O)NC3C4CC5CC(C4)CC3C5)=C2CCCC1 DQMOKQSNSQFVFS-UHFFFAOYSA-N 0.000 claims description 2
YHPGYAAGGFNYJL-ZTDHTWSHSA-N n-[(1s)-2-chloro-1-phenylethyl]-1-(2,4-difluorophenyl)-8-[(4-fluorophenyl)methyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(F)=CC=C1CC1C(N(N=C2C(=O)N[C@H](CCl)C=3C=CC=CC=3)C=3C(=CC(F)=CC=3)F)=C2CCCC1 YHPGYAAGGFNYJL-ZTDHTWSHSA-N 0.000 claims description 2
VUINVTYEJWCWDM-UHFFFAOYSA-N n-benzyl-1-cyclohexyl-8-[(3-fluorophenyl)methyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound FC1=CC=CC(CC2C=3N(C4CCCCC4)N=C(C=3CCCC2)C(=O)NCC=2C=CC=CC=2)=C1 VUINVTYEJWCWDM-UHFFFAOYSA-N 0.000 claims description 2
PRZPIMDDNOHFON-UHFFFAOYSA-N n-benzyl-1-cyclohexyl-8-[(4-fluorophenyl)methyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(F)=CC=C1CC1C(N(C2CCCCC2)N=C2C(=O)NCC=3C=CC=CC=3)=C2CCCC1 PRZPIMDDNOHFON-UHFFFAOYSA-N 0.000 claims description 2
RDPVBRHLZLVYNY-UHFFFAOYSA-N n-benzyl-8-[(4-fluorophenyl)methyl]-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=CC(F)=CC=C1CC1C(NN=C2C(=O)NCC=3C=CC=CC=3)=C2CCCC1 RDPVBRHLZLVYNY-UHFFFAOYSA-N 0.000 claims description 2
QISVRBHCXMQCGH-UHFFFAOYSA-N n-benzyl-8-[(4-fluorophenyl)methyl]-1-methylsulfonyl-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound C1=2CCCCC(CC=3C=CC(F)=CC=3)C=2N(S(=O)(=O)C)N=C1C(=O)NCC1=CC=CC=C1 QISVRBHCXMQCGH-UHFFFAOYSA-N 0.000 claims description 2
JSSYOTIXGSCRLB-UHFFFAOYSA-N n-cyclobutyl-1-(2,4-dichlorophenyl)-8-[(3-fluorophenyl)methyl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound FC1=CC=CC(CC2C=3N(N=C(C=3CCCC2)C(=O)NC2CCC2)C=2C(=CC(Cl)=CC=2)Cl)=C1 JSSYOTIXGSCRLB-UHFFFAOYSA-N 0.000 claims description 2
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 claims description 2
XJEVHMGJSYVQBQ-SECBINFHSA-N (1r)-2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2[C@H](N)CCC2=C1 XJEVHMGJSYVQBQ-SECBINFHSA-N 0.000 claims 1
YFAUASOABRGDBH-KKVCJECGSA-N (8r)-1-cyclohexyl-8-[(3-fluorophenyl)methyl]-n-[(1r,2s)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]-5,6,7,8-tetrahydro-4h-cyclohepta[c]pyrazole-3-carboxamide Chemical compound N([C@@H]1C2=CC=CC=C2C[C@@H]1O)C(=O)C(C=1CCCC[C@H](CC=2C=C(F)C=CC=2)C=11)=NN1C1CCCCC1 YFAUASOABRGDBH-KKVCJECGSA-N 0.000 claims 1
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Classifications

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- C07—ORGANIC CHEMISTRY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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KR1020087009625A 2005-09-23 2006-09-18 헥사하이드로-사이클로헵타피라졸 카나비노이드 모듈레이터 Withdrawn KR20080050522A (ko)

Applications Claiming Priority (2)

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US72025305P	2005-09-23	2005-09-23
US60/720,253		2005-09-23

Publications (1)

Publication Number	Publication Date
KR20080050522A true KR20080050522A (ko)	2008-06-05

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ID=37635790

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Application Number	Title	Priority Date	Filing Date
KR1020087009625A Withdrawn KR20080050522A (ko)	2005-09-23	2006-09-18	헥사하이드로-사이클로헵타피라졸 카나비노이드 모듈레이터

Country Status (24)

Country	Link
US (1)	US20070123578A1 (fr)
EP (1)	EP1937259B1 (fr)
JP (1)	JP2009508953A (fr)
KR (1)	KR20080050522A (fr)
CN (1)	CN101312726A (fr)
AT (1)	ATE534387T1 (fr)
AU (1)	AU2006295121B2 (fr)
BR (1)	BRPI0616402A2 (fr)
CA (1)	CA2623745A1 (fr)
CR (1)	CR9917A (fr)
CY (1)	CY1112426T1 (fr)
DK (1)	DK1937259T3 (fr)
EA (1)	EA200800890A1 (fr)
EC (1)	ECSP088314A (fr)
ES (1)	ES2375213T3 (fr)
HR (1)	HRP20120159T1 (fr)
IL (1)	IL190347A0 (fr)
NO (1)	NO20081948L (fr)
PL (1)	PL1937259T3 (fr)
PT (1)	PT1937259E (fr)
RS (1)	RS52195B (fr)
SI (1)	SI1937259T1 (fr)
WO (1)	WO2007038036A1 (fr)
ZA (1)	ZA200803532B (fr)

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US8378096B2 (en)	2005-09-23	2013-02-19	Janssen Pharmaceutica N.V.	Hexahydro-cycloheptapyrazole cannabinoid modulators
US8378117B2 (en) *	2005-09-23	2013-02-19	Janssen Pharmaceutica N.V.	Hexahydro-cycloheptapyrazole cannabinoid modulators
KR20090120499A (ko) *	2007-03-21	2009-11-24	얀센 파마슈티카 엔.브이.	Ｃｂ２ 수용체 매개 통증의 치료 방법
JP6062633B2 (ja) *	2009-01-28	2017-01-18	カラセラピューティクスインコーポレイテッド	二環式ピラゾロ複素環類
GB201706102D0 (en) *	2017-04-18	2017-05-31	Glaxosmithkline Ip Dev Ltd	Chemical compounds

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US2948718A (en) *		1960-08-09		New n-heterocyclic compounds
DE2460891C2 (de) *	1974-12-21	1982-09-23	Gödecke AG, 1000 Berlin	1-Aminomethyl-1-cycloalkanessigsäuren und deren Ester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
US4087544A (en) *	1974-12-21	1978-05-02	Warner-Lambert Company	Treatment of cranial dysfunctions using novel cyclic amino acids
DK153787C (da) *	1979-06-01	1989-01-16	Wellcome Found	Analogifremgangsmaade til fremstilling af substituerede 3,5-diamino-6-phenyl-1,2,4-triaziner og alfa-cyanobenzyliden-aminoguanidinforbindelser til anvendelse som mellemprodukter herved
LU83729A1 (fr) *	1981-11-04	1983-09-01	Galephar	Sels d'acide valproique,leur preparation et leur utilisation
US4513006A (en) *	1983-09-26	1985-04-23	Mcneil Lab., Inc.	Anticonvulsant sulfamate derivatives
US5242942A (en) *	1992-04-28	1993-09-07	Mcneilab, Inc.	Anticonvulsant fructopyranose cyclic sulfites and sulfates
US5384327A (en) *	1992-12-22	1995-01-24	Mcneilab, Inc.	Anticonvulsant sorbopyranose sulfamates
FR2800375B1 (fr) *	1999-11-03	2004-07-23	Sanofi Synthelabo	Derives tricycliques d'acide pyrazolecarboxylique, leur preparation, les compositions pharmaceutiques en contenant
FR2800372B1 (fr) *	1999-11-03	2001-12-07	Sanofi Synthelabo	Derives tricycliques d'acide 1-benzylpyrazole-3- carboxylique, leur preparation, les medicaments en contenant
US20080249154A1 (en) *	2003-12-26	2008-10-09	Ono Pharmaceutical Co., Ltd.	Preventive and/or Therapeutic Agent For Disease In Which Mitochondrial Benzodiazephine Receptor Participates
AU2005228868B2 (en) *	2004-03-24	2012-02-09	Janssen Pharmaceutica, N.V.	Tetrahydro-indazole cannabinoid modulators
FR2875230A1 (fr) *	2004-09-13	2006-03-17	Sanofi Aventis Sa	Derives de pyrazole condense, leur preparation et leur application en therapeutique

2006
- 2006-09-18 ES ES06814802T patent/ES2375213T3/es active Active
- 2006-09-18 AT AT06814802T patent/ATE534387T1/de active
- 2006-09-18 PT PT06814802T patent/PT1937259E/pt unknown
- 2006-09-18 AU AU2006295121A patent/AU2006295121B2/en not_active Ceased
- 2006-09-18 EP EP06814802A patent/EP1937259B1/fr active Active
- 2006-09-18 DK DK06814802.2T patent/DK1937259T3/da active
- 2006-09-18 RS RS20120064A patent/RS52195B/sr unknown
- 2006-09-18 JP JP2008532297A patent/JP2009508953A/ja active Pending
- 2006-09-18 PL PL06814802T patent/PL1937259T3/pl unknown
- 2006-09-18 SI SI200631246T patent/SI1937259T1/sl unknown
- 2006-09-18 KR KR1020087009625A patent/KR20080050522A/ko not_active Withdrawn
- 2006-09-18 BR BRPI0616402-1A patent/BRPI0616402A2/pt not_active Application Discontinuation
- 2006-09-18 EA EA200800890A patent/EA200800890A1/ru unknown
- 2006-09-18 CN CNA200680043569XA patent/CN101312726A/zh active Pending
- 2006-09-18 CA CA002623745A patent/CA2623745A1/fr not_active Abandoned
- 2006-09-18 US US11/522,771 patent/US20070123578A1/en not_active Abandoned
- 2006-09-18 HR HR20120159T patent/HRP20120159T1/hr unknown
- 2006-09-18 WO PCT/US2006/036158 patent/WO2007038036A1/fr not_active Ceased
2008
- 2008-03-20 IL IL190347A patent/IL190347A0/en unknown
- 2008-03-26 EC EC2008008314A patent/ECSP088314A/es unknown
- 2008-04-22 ZA ZA200803532A patent/ZA200803532B/xx unknown
- 2008-04-23 NO NO20081948A patent/NO20081948L/no not_active Application Discontinuation
- 2008-04-23 CR CR9917A patent/CR9917A/es not_active Application Discontinuation
2012
- 2012-02-09 CY CY20121100138T patent/CY1112426T1/el unknown

Also Published As

Publication number	Publication date
ZA200803532B (en)	2009-09-30
JP2009508953A (ja)	2009-03-05
PT1937259E (pt)	2012-01-17
EA200800890A1 (ru)	2009-02-27
IL190347A0 (en)	2009-09-22
US20070123578A1 (en)	2007-05-31
CR9917A (es)	2008-09-09
CA2623745A1 (fr)	2007-04-05
PL1937259T3 (pl)	2012-04-30
ATE534387T1 (de)	2011-12-15
CN101312726A (zh)	2008-11-26
AU2006295121B2 (en)	2011-10-27
NO20081948L (no)	2008-06-20
ECSP088314A (es)	2008-04-28
DK1937259T3 (da)	2012-02-13
RS52195B (sr)	2012-10-31
AU2006295121A1 (en)	2007-04-05
EP1937259A1 (fr)	2008-07-02
HRP20120159T1 (hr)	2012-03-31
ES2375213T3 (es)	2012-02-27
SI1937259T1 (sl)	2012-02-29
WO2007038036A1 (fr)	2007-04-05
BRPI0616402A2 (pt)	2011-06-21
EP1937259B1 (fr)	2011-11-23
CY1112426T1 (el)	2015-12-09

Publication	Publication Date	Title
US8101592B2 (en)	2012-01-24	Hexahydro-cyclooctyl pyrazole cannabinoid modulators
US20070254911A1 (en)	2007-11-01	Tetrahydro-Pyrazolo[3,4-c]Pyridine Cannabinoid Modulators
US8119621B2 (en)	2012-02-21	Tetrahydro-cyclopentyl pyrazole cannabinoid modulators
JP4942660B2 (ja)	2012-05-30	テトラヒドロピリジニルピラゾールカンナビノイドモジュレーター
KR20080050523A (ko)	2008-06-05	테트라하이드로-인다졸릴 카나비노이드 모듈레이터
KR20100015602A (ko)	2010-02-12	헥사하이드로-사이클로헵타피라졸 카나비노이드 모듈레이터
US8378096B2 (en)	2013-02-19	Hexahydro-cycloheptapyrazole cannabinoid modulators
KR20080050522A (ko)	2008-06-05	헥사하이드로-사이클로헵타피라졸 카나비노이드 모듈레이터
KR20100015607A (ko)	2010-02-12	헥사하이드로-사이클로옥틸 피라졸 카나비노이드 모듈레이터

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2008-04-22	PA0105	International application	Patent event date: 20080422 Patent event code: PA01051R01D Comment text: International Patent Application
2008-06-05	PG1501	Laying open of application
2011-10-19	PC1203	Withdrawal of no request for examination
2011-10-19	WITN	Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid